CN111825549A - Synthesis method of n-butyl glycolate - Google Patents
Synthesis method of n-butyl glycolate Download PDFInfo
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- CN111825549A CN111825549A CN202010732550.8A CN202010732550A CN111825549A CN 111825549 A CN111825549 A CN 111825549A CN 202010732550 A CN202010732550 A CN 202010732550A CN 111825549 A CN111825549 A CN 111825549A
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- glycolate
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- butyl
- butyl glycolate
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- VFGRALUHHHDIQI-UHFFFAOYSA-N butyl 2-hydroxyacetate Chemical compound CCCCOC(=O)CO VFGRALUHHHDIQI-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 238000001308 synthesis method Methods 0.000 title abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 65
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 61
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 17
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 230000009471 action Effects 0.000 claims abstract description 5
- 239000003377 acid catalyst Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 10
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000010189 synthetic method Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 abstract description 12
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000002194 synthesizing effect Effects 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000002910 solid waste Substances 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 20
- 239000007795 chemical reaction product Substances 0.000 description 10
- 238000005070 sampling Methods 0.000 description 5
- 238000012544 monitoring process Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- -1 alpha-H Chemical group 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of chemical synthesis, and particularly discloses a method for synthesizing n-butyl glycolate. The synthesis method of n-butyl glycolate specifically comprises the steps of taking methyl glycolate and n-butanol as reaction raw materials, and heating to 70-150 ℃ to react under the action of an acid catalyst to obtain the n-butyl glycolate. The n-butyl glycolate can be obtained by one-step reaction of methyl glycolate and n-butanol, the whole reaction process is simple to operate, the reaction period is short, the reaction yield is high, the catalyst dosage is small, the synthesis cost of the n-butyl glycolate is remarkably reduced, and the synthesis method of the n-butyl glycolate does not generate tail water or solid waste, and meets the production requirement of environmental protection.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing n-butyl glycolate.
Background
The n-butyl glycolate has functional groups such as alpha-H, hydroxyl, ester group and the like, so that the n-butyl glycolate has chemical properties of alcohol and ester at the same time, and can perform carbonylation reaction, oxidation reaction, hydrolysis reaction, substitution reaction of alpha-H and the like, so that the n-butyl glycolate is not only widely used in various fields such as chemical industry, medicines, feeds, pesticides, dyes, spices and the like, but also widely used as additives of cleaning agents, cosmetics, coatings and the like, and has wide market prospect.
The traditional synthesis method of n-butyl glycolate takes glycolic acid and n-butanol as raw materials and synthesizes the glycolic acid and the n-butanol under the action of an acidic catalyst (a large amount of super acid). Glycolic acid itself has carboxyl and ester groups, so that it can itself be dehydrated and etherified under acidic conditions, and also can itself be subjected to polycondensation, and there are many side reactions, so that the yield and purity of esterification are not high regardless of using concentrated sulfuric acid or other super strong acids as catalysts. In the synthesis process of n-butyl glycolate, the using amount of the super acidic catalyst is larger and reaches about 2.4 of the total amount of glycolic acid and n-butyl alcohol, and the feeding amount of n-butyl alcohol is larger (the feeding amount of n-butyl alcohol is 3-4 times of the mole number of glycolic acid). In the traditional n-butyl glycolate synthesis methods, some of the n-butyl glycolate synthesis methods also gradually reduce the product yield along with the recycling of the ion exchange resin, the discharge of a buffer solution for cleaning and activating the ion exchange resin causes certain pollution to the environment, and the product yield and purity are not obviously improved. Meanwhile, the existing method for synthesizing the glycolic acid adopts hydroxyacetonitrile to sequentially carry out acidolysis and esterification to obtain methyl glycolate, and then the methyl glycolate is hydrolyzed and the methanol is distilled to obtain the glycolic acid.
In conclusion, the existing method for synthesizing n-butyl glycolate has the defects of low synthesis yield, high production cost, complicated operation and inevitable generation of tail water or solid waste in the production process. Because of the increasing environmental protection situation and the increasing market competition, it is important to improve the quality of n-butyl glycolate, reduce the production cost and seek a green and environment-friendly synthesis method for the market.
Disclosure of Invention
Aiming at the problems of low synthesis yield, high production cost, complex operation and generation of a large amount of tail water or solid waste in the existing synthesis method of n-butyl glycolate, the invention provides a synthesis method of n-butyl glycolate.
In order to achieve the purpose of the invention, the embodiment of the invention adopts the following technical scheme:
a synthetic method of n-butyl glycolate specifically uses methyl glycolate and n-butanol as reaction raw materials, and the reaction is carried out by heating to 70-150 ℃ under the action of an acid catalyst.
Compared with the prior art, the synthesis method of n-butyl glycolate provided by the invention is obtained by directly reacting methyl glycolate with n-butanol by heating to 70-150 ℃ under the action of an acid catalyst. Namely, n-butyl glycolate can be obtained by one-step reaction of methyl glycolate and n-butanol, the whole reaction process is simple to operate, the reaction period is short, the selectivity is high, the side reactions are few, the reaction yield is high, the catalyst dosage is small, and the synthesis cost of the n-butyl glycolate is obviously reduced. Meanwhile, the synthetic method of n-butyl glycolate does not generate tail water or solid waste, meets the production requirement of environmental protection, and is suitable for popularization and application.
Preferably, the molar ratio of the methyl glycolate to the n-butanol is 1: 1-2.
Preferably, the acidic catalyst is one of concentrated sulfuric acid, p-toluenesulfonic acid and butyl titanate.
The preferable acidic catalyst can improve the selectivity of the reaction of the methyl glycolate and the n-butanol, ensure the smooth proceeding of the ester exchange reaction, avoid the generation of byproducts and further accelerate the reaction rate of the methyl glycolate and the n-butanol.
Preferably, the acidic catalyst is butyl titanate.
The butyl titanate is used as a catalyst for the reaction of the methyl glycolate and the n-butyl alcohol, so that the reaction period can be obviously shortened, the reaction process is accelerated, and the butyl titanate can ensure that more than 99.9 percent of methyl glycolate reacts to generate n-butyl glycolate under the condition of enough n-butyl alcohol.
Preferably, the amount of the acidic catalyst added is 0.1 to 0.5% by mass based on the mass of the methyl glycolate.
The method selects methyl glycolate and n-butanol as raw materials, and a reaction for synthesizing n-butyl glycolate can be realized by adding a very small amount of catalyst (equivalent to 0.1-0.5% of the mass of the methyl glycolate) at 70-150 ℃.
Preferably, the temperature of the reaction is 110-150 ℃.
The preferable reaction temperature can further shorten the whole reaction period, so that the synthesis process of the n-butyl glycolate is shortened to be within 3-4 h.
Preferably, the methanol produced is withdrawn during the reaction.
The reaction process can be further accelerated by extracting the methanol generated in the reaction process, and the reaction period is shortened.
Preferably, the reaction process is stopped when the mass of the methyl glycolate is less than or equal to 3% of the total mass of the reaction system.
Preferably, after the completion of the reaction, the synthesized n-butyl glycolate is purified.
Preferably, the refining method comprises the following steps: the distillation purification is carried out under vacuum conditions below 600 Pa.
The preferred purification process described above can provide high quality n-butyl glycolate, and the purity of n-butyl glycolate obtained by the purification process can be stabilized to 99.7% or more.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
A synthesis method of n-butyl glycolate comprises heating 1213.04g of methanol aqueous solution (containing 43.749 wt% of methyl glycolate) of methyl glycolate as an intermediate material obtained in a production process of glycolic acid in vacuum, and collecting a mixture of methanol and water to leave 450g of methyl glycolate. 740g of n-butyl alcohol and 0.9g of concentrated sulfuric acid are added into methyl glycolate, the reaction system is heated to 70 ℃, the generated methanol is continuously extracted in the reaction process, the extracted n-butyl alcohol is refluxed, the content of the methyl glycolate in the reaction system is monitored, when the mass of the methyl glycolate is only 0.055% of the total mass of the reaction system, the heating reaction is stopped, and the whole reaction period is 5.2 hours.
Sampling and detecting that the mass of the n-butyl glycolate in the reaction product is 657.36g, namely the conversion rate of the methyl glycolate reaches 99.60 percent.
The reaction product is rectified under the vacuum condition of 600Pa to obtain 658.41g of finished n-butyl glycolate, the purity of the finished n-butyl glycolate reaches 99.79%, and the total yield reaches 99.55%.
Example 2
A method for synthesizing n-butyl glycolate comprises the steps of adding 400g of n-butyl alcohol and 0.5g of butyl titanate into 450g of methyl glycolate, heating a reaction system to 110 ℃, continuously extracting generated methanol in the reaction process, refluxing the extracted n-butyl alcohol, monitoring the content of the methyl glycolate in the reaction system, stopping heating reaction when the mass of the methyl glycolate is only 0.038% of the total mass of the reaction system, and enabling the whole reaction period to be 4.5 hours.
Sampling and detecting that the mass of the n-butyl glycolate in the reaction product is 658.13g, namely the conversion rate of the methyl glycolate reaches 99.72%.
The reaction product is rectified under the vacuum condition of 600Pa to obtain 658.22g of finished n-butyl glycolate, the purity of the finished n-butyl glycolate reaches 99.90 percent, and the yield reaches 99.63 percent.
Example 3
A synthesis method of n-butyl glycolate comprises the steps of adding 440g of n-butanol and 2g of p-toluenesulfonic acid into 450g of methyl glycolate, heating a reaction system to 150 ℃, continuously extracting generated methanol in the reaction process, refluxing the extracted n-butanol, monitoring the content of the methyl glycolate in the reaction system, stopping heating reaction when the mass of the methyl glycolate is only 0.043% of the total mass of the reaction system, and enabling the whole reaction period to be 3.8 hours.
Sampling and detecting that the mass of the n-butyl glycolate in the reaction product is 657.74g, namely the conversion rate of the methyl glycolate reaches 99.66 percent.
The reaction product is rectified under the vacuum condition of 500Pa to obtain 658.15g of finished n-butyl glycolate, the purity of the finished n-butyl glycolate reaches 99.87%, and the yield reaches 99.59%.
Example 4
A method for synthesizing n-butyl glycolate comprises the steps of adding 740g of n-butanol and 1.5g of butyl titanate into 450g of methyl glycolate, heating a reaction system to 140 ℃, continuously extracting generated methanol in the reaction process, refluxing the extracted n-butanol, monitoring the content of the methyl glycolate in the reaction system, stopping heating reaction when the mass of the methyl glycolate is only 0.045% of the total mass of the reaction system, and enabling the whole reaction period to be 4.5 hours.
Sampling and detecting that the mass of the n-butyl glycolate in the reaction product is 659.47g, namely the conversion rate of the methyl glycolate reaches 99.92 percent.
The reaction product is rectified under the vacuum condition of 500Pa to obtain 658.55g of finished n-butyl glycolate, the purity of the finished n-butyl glycolate reaches 99.93 percent, and the total yield reaches 99.71 percent.
Comparative example 1
The methyl glycolate in example 4 was replaced with an equimolar amount of glycolic acid, and other reaction raw materials and conditions were the same as those in example 4. When the mass of the glycolic acid is 4.980% of the total mass of the reaction system, the reduction is not caused, the heating reaction is stopped, and the whole reaction period is 21.0 h.
Sampling and detecting that the mass of the n-butyl glycolate in the reaction product is 551.36g, namely the conversion rate of the methyl glycolate reaches 83.54%.
The reaction product is rectified under the vacuum condition of 500Pa to obtain 635.37g of finished n-butyl glycolate, the purity of the finished n-butyl glycolate reaches 85.49%, and the total yield reaches 82.30%.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents or improvements made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (10)
1. A synthetic method of n-butyl glycolate is characterized by comprising the following steps: the preparation method comprises the steps of taking methyl glycolate and n-butanol as reaction raw materials, and reacting at 70-150 ℃ under the action of an acid catalyst to obtain the methyl glycolate.
2. The process for the synthesis of n-butyl glycolate according to claim 1, characterized in that: the molar ratio of the methyl glycolate to the n-butanol is 1: 1-2.
3. The process for the synthesis of n-butyl glycolate according to claim 1, characterized in that: the acidic catalyst is at least one of concentrated sulfuric acid, p-toluenesulfonic acid and butyl titanate.
4. The process for the synthesis of n-butyl glycolate according to claim 3, characterized in that: the acidic catalyst is butyl titanate.
5. The process for the synthesis of n-butyl glycolate according to claim 1, characterized in that: the amount of the acidic catalyst added is 0.1-0.5% by mass of the methyl glycolate.
6. The process for the synthesis of n-butyl glycolate according to claim 1, characterized in that: the temperature of the reaction is 110-150 ℃.
7. The process for the synthesis of n-butyl glycolate according to claim 1, characterized in that: methanol produced is withdrawn during the reaction.
8. The process for the synthesis of n-butyl glycolate according to claim 1, characterized in that: and stopping the reaction process when the mass of the methyl glycolate is less than or equal to 3 percent of the total mass of the reaction system.
9. The process for the synthesis of n-butyl glycolate according to claim 1, characterized in that: after the reaction is completed, the synthesized n-butyl glycolate is refined.
10. The process for the synthesis of n-butyl glycolate according to claim 9, characterized in that: the refining method comprises the following steps: the distillation purification is carried out under vacuum conditions below 600 Pa.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113387921A (en) * | 2021-06-18 | 2021-09-14 | 华东理工大学 | Method for synthesizing glycolide |
| CN114907208A (en) * | 2022-04-27 | 2022-08-16 | 浙江解氏新材料股份有限公司 | Preparation method of butyl glycolate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111205180A (en) * | 2020-02-13 | 2020-05-29 | 美国吉尔斯股份有限公司 | Preparation method and application of hydroxy acid alkyl ester |
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2020
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111205180A (en) * | 2020-02-13 | 2020-05-29 | 美国吉尔斯股份有限公司 | Preparation method and application of hydroxy acid alkyl ester |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113387921A (en) * | 2021-06-18 | 2021-09-14 | 华东理工大学 | Method for synthesizing glycolide |
| WO2022262712A1 (en) * | 2021-06-18 | 2022-12-22 | 华东理工大学 | Method for synthesizing glycolide |
| CN114907208A (en) * | 2022-04-27 | 2022-08-16 | 浙江解氏新材料股份有限公司 | Preparation method of butyl glycolate |
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